Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: urinary tract infections (UTI) [ICD11:
GC08 
];
infectious gastroenteritis [ICD11:
1A40.Z ];
infection due to Proteus vulgaris [ICD11:
XN118 ]
The structure was elucidated in this paperNCBI PubMed ID: 19651402Publication DOI: 10.1016/j.carres.2009.07.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.N. Kondakova <annakond
gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
O-Polysaccharides were released by mild acid degradation of lipopolysaccharides of Providencia alcalifaciens O35 and Proteus vulgaris O76 and were studied by 1D and 2D (1)H and (13)C NMR spectroscopies, including HMBC and NOESY (ROESY) experiments. Both polysaccharides were found to contain N-(1-carboxyethyl)alanine (alanopine) that is N-linked to 4-amino-4,6-dideoxyglucose. Analysis of published data [Vinogradov, E.; Perry, M. B. Eur. J. Biochem.2000, 267, 2439-2446] shows that alanopine is present also on the same sugar in the lipopolysaccharide core of Proteus mirabilis O6 and O57.
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, Proteus vulgaris, 6-dideoxyglucose, 4-amino-4, Alanopine
Structure type: monomer
Location inside paper: p.2061, chart 1
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, de-O-acetylation, NMR-1D
Comments, role: NMR data for alonopine in O-PS from Providencia alcalifaciens O35. Alanopine was recorded as Ala(2-2)Ala for compatibility with the NMR simulator.
NCBI Taxonomy refs (TaxIDs): 126385,
585
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3
4,2 x?Ala? 175.6 58.4 17.2
4 x?Ala? 171.8 57.2 17.5
?DQuip4N
1H NMR data:
Linkage Residue H1 H2 H3
4,2 x?Ala? - 3.67 1.51
4 x?Ala? - 4.05 1.57
?DQuip4N
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3
4,2 x?Ala? 58.4/3.67 17.2/1.51
4 x?Ala? 57.2/4.05 17.5/1.57
?DQuip4N
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 |
|---|
| 4,2 | x?Ala? |
| 3.67 | 1.51 |
| 4 | x?Ala? |
| 4.05 | 1.57 |
| | ?DQuip4N | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 |
|---|
| 4,2 | x?Ala? | 175.6 | 58.4 | 17.2 |
| 4 | x?Ala? | 171.8 | 57.2 | 17.5 |
| | ?DQuip4N | |
|
There is only one chemically distinct structure:
Found 
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